4-Aminobiphenyl → HCID 2747686, compound

HRID 610427Notes

Reaction equation

HRID 610427 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:21](Cl)(=[O:25])[CH:22]([CH3:24])[CH3:23]>C(Cl)Cl>[C:8]1([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])=[CH:7][CH:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 71024-AminobiphenylHCID 8471TriethylamineHCID 62325Isobutyryl chloride

Product 1

HCID 2747686HCID 2747686, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 4-aminobiphenyl (9.53 g, 56.3 mmol) and triethylamine (5.70 g, 56.3 mmol, 7.85 mL) in methylene chloride (60 mL), cooled to 0° C., was added slowly isobutyryl chloride (6.0 g, 56.3 mmol, 5.90 mL). After stirring at 0° C. for 1 h, the mixture was diluted with methylene chloride (120 mL) and washed with 1N NaOH and saturated brine, then dreid (MgSO4), filtered and concentrated. The residue was washed with ether and dried to provide the title compound as a pale yellow crystalline solid (9.83 g, 73%). 1HNMR (400 MHz, CDCl3 /CD3OD) δ 7.58 (d, 2H), 7.50 (m, 4H), 7.40-7.25 (m, 3H), 2.55-2.49 (m, 1H), 1.18 (d, 6H).

Workup

  1. washwashed with 1N NaOH and saturated brine
  2. filtrationfiltered
  3. concentrationconcentrated
  4. washThe residue was washed with ether
  5. customdried

Sources & evidence

ORD record
ord-dde2b9b2485c4b7f8f6fb327b36cde1f
Source dataset
uspto-grants-1999_12
Patent number
US05998470

Reaction notes

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